N-(3,4-Dimethyl-phen-yl)acetamide.

The conformation of the N-H bond in the title compound (34DMPA), C(10)H(13)NO, is syn to the 3-methyl substituent in the aromatic ring, in contrast to the anti conformation observed with respect to the 3-chloro substituent in N-(3,4-dichloro-phen-yl)acetamide (34DCPA). The asymmetric unit of the structure contains three mol-ecules. The bond parameters in 34DMPA are similar to those in 34DCPA, N-(2,6-dimethyl-phen-yl)acetamide, N-(3,5-dimethyl-phen-yl)acetamide and other acetanilides. The mol-ecules in 34DMPA are linked into infinite chains through N-H⋯O hydrogen bonding.

Related literature

For related literature, see: Gowda et al. (2007a ▶,b ▶); Gowda, Kozisek, Svoboda & Fuess (2007 ▶); Gowda, Kožíšek, Tokarčík & Fuess (2007 ▶); Jones et al. (1990 ▶); Shilpa & Gowda (2007 ▶).

Experimental

Crystal data

C10H13NO

M = 163.21

Triclinic,

a = 6.749 (1) Å

b = 14.281 (2) Å

c = 15.005 (2) Å

α = 85.33 (1)°

β = 79.81 (1)°

γ = 87.58 (1)°

V = 1418.1 (3) Å3

Z = 6

Cu Kα radiation

μ = 0.59 mm−1

T = 299 (2) K

0.35 × 0.33 × 0.18 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: none

5528 measured reflections

5025 independent reflections

3386 reflections with I > 2σ(I)

R int = 0.044

3 standard reflections frequency: 120 min intensity decay: 2.0%

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.210

S = 1.03

5025 reflections

344 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.27 e Å−3

Data collection: CAD-4-PC Software (Enraf–Nonius, 1996 ▶); cell refinement: CAD-4-PC Software; data reduction: REDU4 (Stoe & Cie, 1987 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807060916/lw2051sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807060916/lw2051Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C10H13NO	Z = 6
Mr = 163.21	F000 = 528
Triclinic, P1	Dx = 1.147 Mg m−3
Hall symbol: -P 1	Cu Kα radiation λ = 1.54180 Å
a = 6.749 (1) Å	Cell parameters from 25 reflections
b = 14.281 (2) Å	θ = 3.1–22.1º
c = 15.005 (2) Å	µ = 0.59 mm−1
α = 85.33 (1)º	T = 299 (2) K
β = 79.81 (1)º	Prism, colourless
γ = 87.58 (1)º	0.35 × 0.33 × 0.18 mm
V = 1418.1 (3) Å3

Enraf–Nonius CAD-4 diffractometer	Rint = 0.044
Radiation source: fine-focus sealed tube	θmax = 66.9º
Monochromator: graphite	θmin = 3.0º
T = 299(2) K	h = −8→1
ω/2θ scans	k = −17→17
Absorption correction: none	l = −17→17
5528 measured reflections	3 standard reflections
5025 independent reflections	every 120 min
3386 reflections with I > 2σ(I)	intensity decay: 2.0%

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.064	w = 1/[σ2(Fo2) + (0.1316P)2 + 0.1229P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.210	(Δ/σ)max = 0.001
S = 1.03	Δρmax = 0.26 e Å−3
5025 reflections	Δρmin = −0.27 e Å−3
344 parameters	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0022 (7)
Secondary atom site location: difference Fourier map

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
O1	0.6611 (4)	0.21887 (13)	0.27754 (16)	0.0935 (7)
N1	0.7204 (3)	0.37376 (14)	0.26524 (16)	0.0647 (6)
H1N	0.702 (4)	0.428 (2)	0.2362 (19)	0.078*
C1	0.8633 (4)	0.37519 (17)	0.32314 (17)	0.0633 (6)
C2	1.0021 (4)	0.44579 (19)	0.3073 (2)	0.0713 (7)
H2	1.0045	0.4879	0.2565	0.086*
C3	1.1384 (4)	0.4555 (2)	0.3653 (2)	0.0794 (8)
C4	1.1409 (5)	0.3917 (3)	0.4390 (2)	0.0906 (10)
C5	1.0037 (6)	0.3211 (3)	0.4542 (2)	0.0970 (10)
H5	1.0053	0.2774	0.5036	0.116*
C6	0.8637 (5)	0.3128 (2)	0.3985 (2)	0.0849 (9)
H6	0.7702	0.2654	0.4117	0.102*
C7	0.6247 (4)	0.29887 (17)	0.24731 (19)	0.0658 (6)
C8	0.4682 (4)	0.31912 (19)	0.1893 (2)	0.0778 (8)
H8A	0.4651	0.3850	0.1708	0.093*
H8B	0.3390	0.3016	0.2232	0.093*
H8C	0.4995	0.2838	0.1367	0.093*
C9	1.2754 (5)	0.5374 (3)	0.3480 (3)	0.1155 (13)
H9A	1.2499	0.5751	0.2951	0.139*
H9B	1.4130	0.5149	0.3385	0.139*
H9C	1.2511	0.5747	0.3995	0.139*
C10	1.2889 (7)	0.3980 (4)	0.5030 (3)	0.1352 (18)
H10A	1.4232	0.4007	0.4689	0.162*
H10B	1.2785	0.3437	0.5456	0.162*
H10C	1.2588	0.4537	0.5353	0.162*
O2	0.6415 (3)	0.89842 (12)	0.17410 (15)	0.0810 (6)
N2	0.7398 (3)	1.02533 (14)	0.23505 (15)	0.0625 (5)
H2N	0.709 (4)	1.092 (2)	0.2425 (18)	0.075*
C11	0.9017 (4)	0.98806 (17)	0.27568 (18)	0.0613 (6)
C12	0.9873 (4)	1.04469 (19)	0.32918 (18)	0.0697 (7)
H12	0.9362	1.1057	0.3360	0.084*
C13	1.1444 (5)	1.0139 (2)	0.37231 (19)	0.0775 (8)
C14	1.2212 (4)	0.9219 (2)	0.3629 (2)	0.0810 (8)
C15	1.1404 (5)	0.8675 (2)	0.3084 (3)	0.0908 (10)
H15	1.1927	0.8068	0.3009	0.109*
C16	0.9848 (4)	0.89835 (19)	0.2641 (2)	0.0822 (9)
H16	0.9360	0.8594	0.2267	0.099*
C17	0.6230 (4)	0.98221 (17)	0.18788 (17)	0.0617 (6)
C18	0.4661 (4)	1.04309 (19)	0.1511 (2)	0.0746 (7)
H18A	0.4555	1.1026	0.1774	0.089*
H18B	0.3387	1.0130	0.1660	0.089*
H18C	0.5031	1.0529	0.0863	0.089*
C19	1.2353 (6)	1.0776 (3)	0.4266 (3)	0.1110 (12)
H19A	1.1668	1.1379	0.4254	0.133*
H19B	1.3752	1.0848	0.4013	0.133*
H19C	1.2225	1.0513	0.4882	0.133*
C20	1.3884 (5)	0.8838 (3)	0.4104 (3)	0.1128 (13)
H20A	1.5045	0.9218	0.3914	0.135*
H20B	1.4218	0.8203	0.3953	0.135*
H20C	1.3459	0.8849	0.4748	0.135*
O3	0.6498 (3)	0.55410 (11)	0.16267 (14)	0.0773 (6)
N3	0.5363 (3)	0.70443 (13)	0.14131 (14)	0.0607 (5)
H3N	0.555 (4)	0.760 (2)	0.1545 (18)	0.073*
C21	0.3877 (4)	0.69495 (15)	0.08863 (16)	0.0565 (6)
C22	0.2832 (4)	0.77608 (17)	0.06384 (16)	0.0609 (6)
H22	0.3169	0.8330	0.0823	0.073*
C23	0.1323 (4)	0.7758 (2)	0.01327 (18)	0.0683 (7)
C24	0.0808 (4)	0.6904 (2)	−0.0150 (2)	0.0764 (8)
C25	0.1861 (5)	0.6102 (2)	0.0097 (2)	0.0824 (8)
H25	0.1532	0.5533	−0.0092	0.099*
C26	0.3366 (4)	0.60984 (18)	0.0604 (2)	0.0723 (7)
H26	0.4032	0.5540	0.0756	0.087*
C27	0.6556 (4)	0.63784 (16)	0.17531 (16)	0.0600 (6)
C28	0.7946 (5)	0.67177 (19)	0.2314 (2)	0.0846 (9)
H28A	0.9251	0.6808	0.1947	0.101*
H28B	0.8056	0.6261	0.2810	0.101*
H28C	0.7430	0.7303	0.2546	0.101*
C29	0.0253 (5)	0.8664 (3)	−0.0104 (2)	0.0974 (10)
H29A	−0.1148	0.8630	0.0161	0.117*
H29B	0.0386	0.8766	−0.0752	0.117*
H29C	0.0836	0.9175	0.0127	0.117*
C30	−0.0827 (5)	0.6855 (3)	−0.0706 (2)	0.1065 (12)
H30A	−0.2087	0.7060	−0.0365	0.128*
H30B	−0.0925	0.6218	−0.0854	0.128*
H30C	−0.0511	0.7254	−0.1256	0.128*

	U11	U22	U33	U12	U13	U23
O1	0.1197 (17)	0.0455 (10)	0.1293 (18)	0.0036 (10)	−0.0624 (14)	−0.0039 (10)
N1	0.0750 (14)	0.0435 (10)	0.0809 (14)	0.0084 (9)	−0.0294 (11)	−0.0085 (9)
C1	0.0722 (16)	0.0520 (13)	0.0701 (15)	0.0128 (11)	−0.0214 (13)	−0.0183 (11)
C2	0.0703 (16)	0.0615 (15)	0.0851 (18)	0.0085 (12)	−0.0187 (14)	−0.0180 (13)
C3	0.0669 (17)	0.0801 (19)	0.095 (2)	0.0081 (14)	−0.0113 (15)	−0.0384 (16)
C4	0.094 (2)	0.107 (3)	0.078 (2)	0.0302 (19)	−0.0285 (17)	−0.0381 (19)
C5	0.128 (3)	0.095 (2)	0.0727 (19)	0.019 (2)	−0.033 (2)	−0.0118 (17)
C6	0.112 (2)	0.0733 (18)	0.0740 (17)	0.0072 (16)	−0.0310 (17)	−0.0088 (14)
C7	0.0712 (15)	0.0480 (13)	0.0822 (17)	0.0085 (11)	−0.0229 (13)	−0.0134 (11)
C8	0.0755 (17)	0.0617 (15)	0.104 (2)	0.0046 (13)	−0.0362 (16)	−0.0142 (14)
C9	0.092 (2)	0.126 (3)	0.133 (3)	−0.020 (2)	−0.015 (2)	−0.041 (3)
C10	0.125 (3)	0.190 (5)	0.109 (3)	0.038 (3)	−0.060 (3)	−0.061 (3)
O2	0.0835 (13)	0.0536 (10)	0.1117 (15)	−0.0016 (9)	−0.0232 (11)	−0.0266 (10)
N2	0.0678 (12)	0.0451 (10)	0.0776 (13)	−0.0025 (9)	−0.0202 (11)	−0.0051 (9)
C11	0.0581 (13)	0.0532 (13)	0.0713 (15)	−0.0023 (10)	−0.0100 (12)	0.0011 (11)
C12	0.0714 (16)	0.0664 (16)	0.0741 (16)	0.0001 (12)	−0.0187 (14)	−0.0102 (12)
C13	0.0732 (17)	0.094 (2)	0.0659 (16)	−0.0067 (15)	−0.0133 (14)	−0.0036 (14)
C14	0.0640 (16)	0.089 (2)	0.0840 (19)	0.0010 (15)	−0.0099 (15)	0.0200 (16)
C15	0.0762 (19)	0.0631 (17)	0.132 (3)	0.0055 (14)	−0.0238 (19)	0.0067 (18)
C16	0.0772 (18)	0.0521 (14)	0.122 (2)	0.0023 (12)	−0.0285 (18)	−0.0108 (15)
C17	0.0597 (14)	0.0531 (13)	0.0713 (15)	−0.0071 (10)	−0.0063 (12)	−0.0077 (11)
C18	0.0770 (17)	0.0628 (15)	0.0889 (19)	−0.0060 (13)	−0.0286 (15)	−0.0025 (13)
C19	0.108 (3)	0.130 (3)	0.107 (3)	0.004 (2)	−0.044 (2)	−0.030 (2)
C20	0.088 (2)	0.131 (3)	0.116 (3)	0.004 (2)	−0.029 (2)	0.033 (2)
O3	0.0991 (14)	0.0402 (9)	0.1004 (14)	0.0032 (8)	−0.0406 (11)	−0.0032 (8)
N3	0.0747 (13)	0.0378 (10)	0.0753 (13)	0.0002 (9)	−0.0272 (11)	−0.0072 (9)
C21	0.0622 (14)	0.0466 (12)	0.0624 (13)	0.0019 (10)	−0.0150 (11)	−0.0074 (10)
C22	0.0681 (15)	0.0503 (12)	0.0650 (14)	0.0039 (10)	−0.0144 (12)	−0.0051 (10)
C23	0.0603 (14)	0.0786 (17)	0.0635 (15)	0.0098 (12)	−0.0093 (12)	−0.0006 (12)
C24	0.0604 (15)	0.098 (2)	0.0734 (17)	0.0008 (14)	−0.0160 (13)	−0.0144 (15)
C25	0.085 (2)	0.0730 (18)	0.098 (2)	−0.0096 (15)	−0.0327 (17)	−0.0188 (15)
C26	0.0814 (18)	0.0517 (14)	0.0914 (19)	−0.0013 (12)	−0.0318 (15)	−0.0141 (12)
C27	0.0740 (15)	0.0439 (12)	0.0643 (14)	−0.0023 (10)	−0.0202 (12)	0.0016 (10)
C28	0.111 (2)	0.0558 (15)	0.099 (2)	0.0038 (14)	−0.0545 (19)	−0.0015 (14)
C29	0.085 (2)	0.104 (2)	0.100 (2)	0.0300 (18)	−0.0245 (18)	0.0084 (19)
C30	0.076 (2)	0.159 (4)	0.093 (2)	0.002 (2)	−0.0321 (18)	−0.026 (2)

O1—C7	1.226 (3)	C15—H15	0.9300
N1—C7	1.342 (3)	C16—H16	0.9300
N1—C1	1.410 (3)	C17—C18	1.494 (4)
N1—H1N	0.88 (3)	C18—H18A	0.9600
C1—C6	1.382 (4)	C18—H18B	0.9600
C1—C2	1.383 (4)	C18—H18C	0.9600
C2—C3	1.391 (4)	C19—H19A	0.9600
C2—H2	0.9300	C19—H19B	0.9600
C3—C4	1.376 (5)	C19—H19C	0.9600
C3—C9	1.500 (5)	C20—H20A	0.9600
C4—C5	1.376 (5)	C20—H20B	0.9600
C4—C10	1.514 (4)	C20—H20C	0.9600
C5—C6	1.382 (4)	O3—C27	1.229 (3)
C5—H5	0.9300	N3—C27	1.347 (3)
C6—H6	0.9300	N3—C21	1.399 (3)
C7—C8	1.488 (4)	N3—H3N	0.86 (3)
C8—H8A	0.9600	C21—C22	1.390 (3)
C8—H8B	0.9600	C21—C26	1.395 (3)
C8—H8C	0.9600	C22—C23	1.374 (4)
C9—H9A	0.9600	C22—H22	0.9300
C9—H9B	0.9600	C23—C24	1.400 (4)
C9—H9C	0.9600	C23—C29	1.503 (4)
C10—H10A	0.9600	C24—C25	1.382 (4)
C10—H10B	0.9600	C24—C30	1.504 (4)
C10—H10C	0.9600	C25—C26	1.372 (4)
O2—C17	1.228 (3)	C25—H25	0.9300
N2—C17	1.346 (3)	C26—H26	0.9300
N2—C11	1.408 (3)	C27—C28	1.486 (4)
N2—H2N	0.98 (3)	C28—H28A	0.9600
C11—C16	1.388 (4)	C28—H28B	0.9600
C11—C12	1.393 (4)	C28—H28C	0.9600
C12—C13	1.376 (4)	C29—H29A	0.9600
C12—H12	0.9300	C29—H29B	0.9600
C13—C14	1.401 (5)	C29—H29C	0.9600
C13—C19	1.487 (4)	C30—H30A	0.9600
C14—C15	1.366 (5)	C30—H30B	0.9600
C14—C20	1.499 (4)	C30—H30C	0.9600
C15—C16	1.378 (4)
C7—N1—C1	127.2 (2)	O2—C17—N2	123.6 (2)
C7—N1—H1N	119.3 (19)	O2—C17—C18	120.6 (2)
C1—N1—H1N	113.3 (19)	N2—C17—C18	115.8 (2)
C6—C1—C2	118.2 (3)	C17—C18—H18A	109.5
C6—C1—N1	123.0 (3)	C17—C18—H18B	109.5
C2—C1—N1	118.6 (2)	H18A—C18—H18B	109.5
C1—C2—C3	121.8 (3)	C17—C18—H18C	109.5
C1—C2—H2	119.1	H18A—C18—H18C	109.5
C3—C2—H2	119.1	H18B—C18—H18C	109.5
C4—C3—C2	119.6 (3)	C13—C19—H19A	109.5
C4—C3—C9	121.2 (3)	C13—C19—H19B	109.5
C2—C3—C9	119.2 (3)	H19A—C19—H19B	109.5
C5—C4—C3	118.5 (3)	C13—C19—H19C	109.5
C5—C4—C10	119.9 (4)	H19A—C19—H19C	109.5
C3—C4—C10	121.7 (4)	H19B—C19—H19C	109.5
C4—C5—C6	122.2 (3)	C14—C20—H20A	109.5
C4—C5—H5	118.9	C14—C20—H20B	109.5
C6—C5—H5	118.9	H20A—C20—H20B	109.5
C1—C6—C5	119.7 (3)	C14—C20—H20C	109.5
C1—C6—H6	120.2	H20A—C20—H20C	109.5
C5—C6—H6	120.2	H20B—C20—H20C	109.5
O1—C7—N1	122.5 (2)	C27—N3—C21	129.3 (2)
O1—C7—C8	121.8 (2)	C27—N3—H3N	114.5 (19)
N1—C7—C8	115.7 (2)	C21—N3—H3N	116.2 (18)
C7—C8—H8A	109.5	C22—C21—C26	118.2 (2)
C7—C8—H8B	109.5	C22—C21—N3	117.3 (2)
H8A—C8—H8B	109.5	C26—C21—N3	124.5 (2)
C7—C8—H8C	109.5	C23—C22—C21	122.9 (2)
H8A—C8—H8C	109.5	C23—C22—H22	118.6
H8B—C8—H8C	109.5	C21—C22—H22	118.6
C3—C9—H9A	109.5	C22—C23—C24	119.0 (2)
C3—C9—H9B	109.5	C22—C23—C29	119.8 (3)
H9A—C9—H9B	109.5	C24—C23—C29	121.2 (3)
C3—C9—H9C	109.5	C25—C24—C23	117.7 (3)
H9A—C9—H9C	109.5	C25—C24—C30	120.7 (3)
H9B—C9—H9C	109.5	C23—C24—C30	121.5 (3)
C4—C10—H10A	109.5	C26—C25—C24	123.7 (3)
C4—C10—H10B	109.5	C26—C25—H25	118.2
H10A—C10—H10B	109.5	C24—C25—H25	118.2
C4—C10—H10C	109.5	C25—C26—C21	118.6 (3)
H10A—C10—H10C	109.5	C25—C26—H26	120.7
H10B—C10—H10C	109.5	C21—C26—H26	120.7
C17—N2—C11	129.2 (2)	O3—C27—N3	123.1 (2)
C17—N2—H2N	116.1 (16)	O3—C27—C28	121.4 (2)
C11—N2—H2N	114.7 (16)	N3—C27—C28	115.5 (2)
C16—C11—C12	117.6 (3)	C27—C28—H28A	109.5
C16—C11—N2	123.8 (2)	C27—C28—H28B	109.5
C12—C11—N2	118.5 (2)	H28A—C28—H28B	109.5
C13—C12—C11	122.6 (3)	C27—C28—H28C	109.5
C13—C12—H12	118.7	H28A—C28—H28C	109.5
C11—C12—H12	118.7	H28B—C28—H28C	109.5
C12—C13—C14	119.0 (3)	C23—C29—H29A	109.5
C12—C13—C19	120.8 (3)	C23—C29—H29B	109.5
C14—C13—C19	120.1 (3)	H29A—C29—H29B	109.5
C15—C14—C13	118.1 (3)	C23—C29—H29C	109.5
C15—C14—C20	120.5 (3)	H29A—C29—H29C	109.5
C13—C14—C20	121.3 (3)	H29B—C29—H29C	109.5
C14—C15—C16	123.1 (3)	C24—C30—H30A	109.5
C14—C15—H15	118.5	C24—C30—H30B	109.5
C16—C15—H15	118.5	H30A—C30—H30B	109.5
C15—C16—C11	119.5 (3)	C24—C30—H30C	109.5
C15—C16—H16	120.3	H30A—C30—H30C	109.5
C11—C16—H16	120.3	H30B—C30—H30C	109.5
C7—N1—C1—C6	−29.7 (4)	C19—C13—C14—C20	3.1 (5)
C7—N1—C1—C2	154.5 (3)	C13—C14—C15—C16	−1.3 (5)
C6—C1—C2—C3	−0.6 (4)	C20—C14—C15—C16	179.1 (3)
N1—C1—C2—C3	175.4 (2)	C14—C15—C16—C11	−1.2 (5)
C1—C2—C3—C4	2.2 (4)	C12—C11—C16—C15	2.9 (4)
C1—C2—C3—C9	−175.8 (3)	N2—C11—C16—C15	−178.6 (3)
C2—C3—C4—C5	−1.6 (4)	C11—N2—C17—O2	1.1 (4)
C9—C3—C4—C5	176.3 (3)	C11—N2—C17—C18	−178.3 (2)
C2—C3—C4—C10	178.8 (3)	C27—N3—C21—C22	178.8 (2)
C9—C3—C4—C10	−3.3 (5)	C27—N3—C21—C26	−0.5 (4)
C3—C4—C5—C6	−0.5 (5)	C26—C21—C22—C23	0.2 (4)
C10—C4—C5—C6	179.2 (3)	N3—C21—C22—C23	−179.1 (2)
C2—C1—C6—C5	−1.4 (4)	C21—C22—C23—C24	−0.1 (4)
N1—C1—C6—C5	−177.3 (3)	C21—C22—C23—C29	179.6 (3)
C4—C5—C6—C1	2.0 (5)	C22—C23—C24—C25	−0.1 (4)
C1—N1—C7—O1	−4.0 (5)	C29—C23—C24—C25	−179.9 (3)
C1—N1—C7—C8	175.1 (2)	C22—C23—C24—C30	−179.9 (3)
C17—N2—C11—C16	7.9 (4)	C29—C23—C24—C30	0.4 (4)
C17—N2—C11—C12	−173.6 (3)	C23—C24—C25—C26	0.3 (5)
C16—C11—C12—C13	−2.1 (4)	C30—C24—C25—C26	−179.9 (3)
N2—C11—C12—C13	179.3 (2)	C24—C25—C26—C21	−0.3 (5)
C11—C12—C13—C14	−0.4 (4)	C22—C21—C26—C25	0.0 (4)
C11—C12—C13—C19	178.2 (3)	N3—C21—C26—C25	179.3 (3)
C12—C13—C14—C15	2.1 (4)	C21—N3—C27—O3	0.7 (4)
C19—C13—C14—C15	−176.5 (3)	C21—N3—C27—C28	−178.2 (3)
C12—C13—C14—C20	−178.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3	0.88 (3)	2.08 (3)	2.956 (3)	177 (3)
N3—H3N···O2	0.86 (3)	2.14 (3)	2.989 (3)	172 (3)
N2—H2N···O1i	0.98 (3)	1.92 (3)	2.893 (3)	170 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3	0.88 (3)	2.08 (3)	2.956 (3)	177 (3)
N3—H3N⋯O2	0.86 (3)	2.14 (3)	2.989 (3)	172 (3)
N2—H2N⋯O1i	0.98 (3)	1.92 (3)	2.893 (3)	170 (2)

Symmetry code: (i) .